TY  - THES
AU  - Jovanović, Miloš
PY  - 2020
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7643
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:22722/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=18382089
UR  - https://nardus.mpn.gov.rs/handle/123456789/17505
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3720
AB  - Ramnolipidi su ekološki prihvatljivi biosurfaktanti koje proizvodi bakterija Pseudomonas aeruginosa. Zbog interesantnog biološkog profila i odličnih fizičko-hemijskih svojstava nalaze primenu u biotehnologiji, bioremedijaciji i medicini. Njihova šira i ekonomski prihvatljivija primena je međutim značajno otežana činjenicom da se teško mogu dobiti u većim količinama i u čistoj formi. Kao posledica toga istraživanja u smeru strukturnih modifikacija i sinteze analoga ramnolipida nisu još uvek zaživela, samim tim, fizičko-hemijska i biološka svojstva srodnih molekula nisu još uvek dovoljno istražena. Imajuči u vidu neekonomičnost sinteze ramnolipida cilj ovog istraživanja bio je pronaći sintetski pristupačne molekule koji bi imali isti ili bolji biološki ili fizičko-hemijski profil od samih prirodnih ramnolipida. Korišćenjem (R)-3-hidroksikiseline kao osnovnog strukturnog fragmenta sintetisani su šećerni, heterociklični i peptidni analozi ramnolipida i ispitivane njihove fizičko-hemijske i antimikrobne osobine. Zamenom ramnoze drugim šećerima smanjuje se cena proizvodnje ovih molekula dok se istovremeno očuvava površinska aktivnost i biorazgradivost. Zamenom ramnoze peptidima dobijajena je serija jedinjenja sa anti-adhezivnim dejstvom na Candida albicans (BFIC50 = 4,5 μg/mL). Najaktivniji derivati su konjugati leucina i 3-hidroksikiselina koje sadrže benzil estar. SAR studijom je pokazano da je optimalan broj aminokiselina u bočnom nizu 1-2, kao i da se anti-biofilm aktivnost povećava sa produženjem alifatičnog niza 3-hidroksikiselina. Ova jedinjenja inhibiraju formiranje biofilma sprečavanjem adhezije C. albicans na abiotsku i biološku površinu.Pored ramnolipida, i mali molekuli koji pripadaju bromopirolskim alkaloidima takođe ispoljavaju antimikrobna i anti-biofilm svojstva. Longamid B je jedan od naistraživanijih molekula ove grupe. Poznata je njegova antimikrobna aktivnost na bakterijske sojeve Bacillus subtilis i Staphylococcus aureus. Iz tog razloga predstavlja atraktivan target za totalnu sintezu i šire proučavanje hemijskog prostora definisanog njegovom strukturom. Pretpostavljeno je da se osnovni skelet bromopirolskih alkaloida, može dobiti intramolekulskom nukleofilnom adicijom na alene. Ispitivanjem ciklizacionih reakcija aminoalena u prisustvu serije metalnih soli došlo se do optimalnih uslova koji su podrazumevali korišćenje stehiometrijske količine AgNO3. Zahvaljujući hiralnom ciklizacionom prekursoru reakcija ciklizacije se odvijala stereoselektivno. Razvijena metodologija iskorišćena je u sintezi longamida B i stilizina D.U cilju diverzifikacije strukture bromopirolskih alkaloida ispitivane su reakcije i karboaminacije aminoalena katalizovane paladijumom. Ova strategija omogućila je sintezu α-supstituisanih derivata longamida.
AB  - Rhamnolipids are environmentally friendly biosurfactants produced mostly by strains of Pseudomonas aeruginosa. Due to their interesting biological profile and excellent physico-chemical properties, they find application in biotechnology, bioremediation and medicine. The inefficient large scale production, however, still hinders their wider application. Consequently, the research on structural modifications and the synthesis of rhamnolipid analogues is still in the early stages and the physico-chemical and biological properties of related molecules are not yet fully explored. Thus this research aimed to find synthetically accessible molecules which would mimic or enhance the properties of the parent molecule. Using (R)-hydroxy acids as a core building block, the sugar, heterocyclic and peptide analogues of rhamnolipids were synthesised and their physico-chemical and antimicrobial properties evaluated. Replacing rhamnose with other sugars allows for a reduction in production cost whilst preserving the surface active properties and biodegradability of the parent molecules. The replacement of rhamnose with peptides produced a series of molecules with anti-adhesion effect on Candida albicans (BFIC50 = 4,5 μg/mL). The most potent derivatives were conjugates of leucine and benzyl esters of 3-hydroxyacids. The SAR study showed that the optimal number of amino acids in the sidechain was one or two, furthermore, the elongation of the aliphatic chain also improved the anti-biofilm properties of the peptide derivatives. The compounds were found to exert anti-biofilm properties through inhibition of C. albicans adhesion to abiotic and biotic surfaces.Apart from rhamnolipids, small molecules, members of bromopyrrole alkaloid family, also exert antimicrobial and anti-biofilm properties. Longamid B is one of the most studied molecules of this group. Its antimicrobial activity against Bacillus subtilis and Staphylococcus aureus is well known. Therefore it represents an attractive target for total synthesis and the exploration of chemical space around the molecule. Our envisaged strategy was based on the hypothesis that the core structure of bromopyrrole alkaloids could be accessed via intramolecular nucleophilic addition to allene moiety. The investigation of cyclization reactions of aminoallenes in the presence of a series of metal salts uncovered a stoichiometric amount of AgNO3 as the best option for the reaction. The chiral precursor allowed a stereoselective cyclization process. The developed methodology was successfully applied in the synthesis of longamide B and stylisine D.With the aim of diversificating the structure of bromopyrrole alkaloids the carboamination reactions of aminoallenes catalyzed by palladium were also explored. This strategy allowed the synthesis of α-substituted derivatives of longamide B.
PB  - Универзитет у Београду, Фармацеутски факултет
T2  - Универзитет у Београду
T1  - Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija
UR  - https://hdl.handle.net/21.15107/rcub_nardus_17505
ER  - 

@phdthesis{
author = "Jovanović, Miloš",
year = "2020",
abstract = "Ramnolipidi su ekološki prihvatljivi biosurfaktanti koje proizvodi bakterija Pseudomonas aeruginosa. Zbog interesantnog biološkog profila i odličnih fizičko-hemijskih svojstava nalaze primenu u biotehnologiji, bioremedijaciji i medicini. Njihova šira i ekonomski prihvatljivija primena je međutim značajno otežana činjenicom da se teško mogu dobiti u većim količinama i u čistoj formi. Kao posledica toga istraživanja u smeru strukturnih modifikacija i sinteze analoga ramnolipida nisu još uvek zaživela, samim tim, fizičko-hemijska i biološka svojstva srodnih molekula nisu još uvek dovoljno istražena. Imajuči u vidu neekonomičnost sinteze ramnolipida cilj ovog istraživanja bio je pronaći sintetski pristupačne molekule koji bi imali isti ili bolji biološki ili fizičko-hemijski profil od samih prirodnih ramnolipida. Korišćenjem (R)-3-hidroksikiseline kao osnovnog strukturnog fragmenta sintetisani su šećerni, heterociklični i peptidni analozi ramnolipida i ispitivane njihove fizičko-hemijske i antimikrobne osobine. Zamenom ramnoze drugim šećerima smanjuje se cena proizvodnje ovih molekula dok se istovremeno očuvava površinska aktivnost i biorazgradivost. Zamenom ramnoze peptidima dobijajena je serija jedinjenja sa anti-adhezivnim dejstvom na Candida albicans (BFIC50 = 4,5 μg/mL). Najaktivniji derivati su konjugati leucina i 3-hidroksikiselina koje sadrže benzil estar. SAR studijom je pokazano da je optimalan broj aminokiselina u bočnom nizu 1-2, kao i da se anti-biofilm aktivnost povećava sa produženjem alifatičnog niza 3-hidroksikiselina. Ova jedinjenja inhibiraju formiranje biofilma sprečavanjem adhezije C. albicans na abiotsku i biološku površinu.Pored ramnolipida, i mali molekuli koji pripadaju bromopirolskim alkaloidima takođe ispoljavaju antimikrobna i anti-biofilm svojstva. Longamid B je jedan od naistraživanijih molekula ove grupe. Poznata je njegova antimikrobna aktivnost na bakterijske sojeve Bacillus subtilis i Staphylococcus aureus. Iz tog razloga predstavlja atraktivan target za totalnu sintezu i šire proučavanje hemijskog prostora definisanog njegovom strukturom. Pretpostavljeno je da se osnovni skelet bromopirolskih alkaloida, može dobiti intramolekulskom nukleofilnom adicijom na alene. Ispitivanjem ciklizacionih reakcija aminoalena u prisustvu serije metalnih soli došlo se do optimalnih uslova koji su podrazumevali korišćenje stehiometrijske količine AgNO3. Zahvaljujući hiralnom ciklizacionom prekursoru reakcija ciklizacije se odvijala stereoselektivno. Razvijena metodologija iskorišćena je u sintezi longamida B i stilizina D.U cilju diverzifikacije strukture bromopirolskih alkaloida ispitivane su reakcije i karboaminacije aminoalena katalizovane paladijumom. Ova strategija omogućila je sintezu α-supstituisanih derivata longamida., Rhamnolipids are environmentally friendly biosurfactants produced mostly by strains of Pseudomonas aeruginosa. Due to their interesting biological profile and excellent physico-chemical properties, they find application in biotechnology, bioremediation and medicine. The inefficient large scale production, however, still hinders their wider application. Consequently, the research on structural modifications and the synthesis of rhamnolipid analogues is still in the early stages and the physico-chemical and biological properties of related molecules are not yet fully explored. Thus this research aimed to find synthetically accessible molecules which would mimic or enhance the properties of the parent molecule. Using (R)-hydroxy acids as a core building block, the sugar, heterocyclic and peptide analogues of rhamnolipids were synthesised and their physico-chemical and antimicrobial properties evaluated. Replacing rhamnose with other sugars allows for a reduction in production cost whilst preserving the surface active properties and biodegradability of the parent molecules. The replacement of rhamnose with peptides produced a series of molecules with anti-adhesion effect on Candida albicans (BFIC50 = 4,5 μg/mL). The most potent derivatives were conjugates of leucine and benzyl esters of 3-hydroxyacids. The SAR study showed that the optimal number of amino acids in the sidechain was one or two, furthermore, the elongation of the aliphatic chain also improved the anti-biofilm properties of the peptide derivatives. The compounds were found to exert anti-biofilm properties through inhibition of C. albicans adhesion to abiotic and biotic surfaces.Apart from rhamnolipids, small molecules, members of bromopyrrole alkaloid family, also exert antimicrobial and anti-biofilm properties. Longamid B is one of the most studied molecules of this group. Its antimicrobial activity against Bacillus subtilis and Staphylococcus aureus is well known. Therefore it represents an attractive target for total synthesis and the exploration of chemical space around the molecule. Our envisaged strategy was based on the hypothesis that the core structure of bromopyrrole alkaloids could be accessed via intramolecular nucleophilic addition to allene moiety. The investigation of cyclization reactions of aminoallenes in the presence of a series of metal salts uncovered a stoichiometric amount of AgNO3 as the best option for the reaction. The chiral precursor allowed a stereoselective cyclization process. The developed methodology was successfully applied in the synthesis of longamide B and stylisine D.With the aim of diversificating the structure of bromopyrrole alkaloids the carboamination reactions of aminoallenes catalyzed by palladium were also explored. This strategy allowed the synthesis of α-substituted derivatives of longamide B.",
publisher = "Универзитет у Београду, Фармацеутски факултет",
journal = "Универзитет у Београду",
title = "Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija",
url = "https://hdl.handle.net/21.15107/rcub_nardus_17505"
}

Jovanović, M.. (2020). Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija. in Универзитет у Београду
Универзитет у Београду, Фармацеутски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_17505

Jovanović M. Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija. in Универзитет у Београду. 2020;.
https://hdl.handle.net/21.15107/rcub_nardus_17505 .

Jovanović, Miloš, "Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija" in Универзитет у Београду (2020),
https://hdl.handle.net/21.15107/rcub_nardus_17505 .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Erić, Slavica
AU  - Savić, Vladimir
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3481
AB  - Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag-catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.
PB  - Wiley-Blackwell
T2  - European Journal of Organic Chemistry
T1  - Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives
VL  - 2020
IS  - 3
SP  - 295
EP  - 305
DO  - 10.1002/ejoc.201901554
ER  - 

@article{
author = "Jovanović, Miloš and Petković, Miloš and Jovanović, Predrag and Simić, Milena and Tasić, Gordana and Erić, Slavica and Savić, Vladimir",
year = "2020",
abstract = "Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag-catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.",
publisher = "Wiley-Blackwell",
journal = "European Journal of Organic Chemistry",
title = "Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives",
volume = "2020",
number = "3",
pages = "295-305",
doi = "10.1002/ejoc.201901554"
}

Jovanović, M., Petković, M., Jovanović, P., Simić, M., Tasić, G., Erić, S.,& Savić, V.. (2020). Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives. in European Journal of Organic Chemistry
Wiley-Blackwell., 2020(3), 295-305.
https://doi.org/10.1002/ejoc.201901554

Jovanović M, Petković M, Jovanović P, Simić M, Tasić G, Erić S, Savić V. Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives. in European Journal of Organic Chemistry. 2020;2020(3):295-305.
doi:10.1002/ejoc.201901554 .

Jovanović, Miloš, Petković, Miloš, Jovanović, Predrag, Simić, Milena, Tasić, Gordana, Erić, Slavica, Savić, Vladimir, "Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives" in European Journal of Organic Chemistry, 2020, no. 3 (2020):295-305,
https://doi.org/10.1002/ejoc.201901554 . .

TY  - CONF
AU  - Simić, Milena
AU  - Micić, Nikola
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Jovanović, Miloš
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5384
AB  - Tetracyclic octahydro-dipyrroloquinoline architecture is not commonly found in natural
products but some of them such as Incargranine B isolated from Incarvillea mairei var.
grandiflora and seneciobipyrrolidine isolated from Senecio scandens are derivatives of this
heterocycle [1-3], Figure 1. We envisaged potential synthetic pathway for this skeleton
based around two key steps: (3+2) dipolar cycloaddition of azomethine ylides and
unsaturated ketone and intramolecular Cu (I)-catalyzed amination to form the core
structure (Scheme 1). Creation of several chiral atoms during this process prompted careful
structural examination in order to establish correct stereochemistry and correlate it with
the structure of natural products.
PB  - Bruker BioSpin
C3  - 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts
T1  - Structural studies of model system for seneciobipyrrolidine skeleton synthesis
SP  - 52
EP  - 52
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5384
ER  - 

@conference{
author = "Simić, Milena and Micić, Nikola and Petković, Miloš and Jovanović, Predrag and Tasić, Gordana and Jovanović, Miloš and Savić, Vladimir",
year = "2019",
abstract = "Tetracyclic octahydro-dipyrroloquinoline architecture is not commonly found in natural
products but some of them such as Incargranine B isolated from Incarvillea mairei var.
grandiflora and seneciobipyrrolidine isolated from Senecio scandens are derivatives of this
heterocycle [1-3], Figure 1. We envisaged potential synthetic pathway for this skeleton
based around two key steps: (3+2) dipolar cycloaddition of azomethine ylides and
unsaturated ketone and intramolecular Cu (I)-catalyzed amination to form the core
structure (Scheme 1). Creation of several chiral atoms during this process prompted careful
structural examination in order to establish correct stereochemistry and correlate it with
the structure of natural products.",
publisher = "Bruker BioSpin",
journal = "21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts",
title = "Structural studies of model system for seneciobipyrrolidine skeleton synthesis",
pages = "52-52",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5384"
}

Simić, M., Micić, N., Petković, M., Jovanović, P., Tasić, G., Jovanović, M.,& Savić, V.. (2019). Structural studies of model system for seneciobipyrrolidine skeleton synthesis. in 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts
Bruker BioSpin., 52-52.
https://hdl.handle.net/21.15107/rcub_farfar_5384

Simić M, Micić N, Petković M, Jovanović P, Tasić G, Jovanović M, Savić V. Structural studies of model system for seneciobipyrrolidine skeleton synthesis. in 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts. 2019;:52-52.
https://hdl.handle.net/21.15107/rcub_farfar_5384 .

Simić, Milena, Micić, Nikola, Petković, Miloš, Jovanović, Predrag, Tasić, Gordana, Jovanović, Miloš, Savić, Vladimir, "Structural studies of model system for seneciobipyrrolidine skeleton synthesis" in 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts (2019):52-52,
https://hdl.handle.net/21.15107/rcub_farfar_5384 .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Simić, Milena
AU  - Jovanović, Miloš
AU  - Tasić, Gordana
AU  - Crnogorac, Marija Dj.
AU  - Žižak, Željko
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5329
AB  - A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.
PB  - Wiley-VCH Verlag
T2  - European Journal of Organic Chemistry
T1  - Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals
VL  - 2019
IS  - 29
SP  - 4701
EP  - 4709
DO  - 10.1002/ejoc.201900672
ER  - 

@article{
author = "Jovanović, Predrag and Petković, Miloš and Simić, Milena and Jovanović, Miloš and Tasić, Gordana and Crnogorac, Marija Dj. and Žižak, Željko and Savić, Vladimir",
year = "2019",
abstract = "A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.",
publisher = "Wiley-VCH Verlag",
journal = "European Journal of Organic Chemistry",
title = "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals",
volume = "2019",
number = "29",
pages = "4701-4709",
doi = "10.1002/ejoc.201900672"
}

Jovanović, P., Petković, M., Simić, M., Jovanović, M., Tasić, G., Crnogorac, M. Dj., Žižak, Ž.,& Savić, V.. (2019). Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry
Wiley-VCH Verlag., 2019(29), 4701-4709.
https://doi.org/10.1002/ejoc.201900672

Jovanović P, Petković M, Simić M, Jovanović M, Tasić G, Crnogorac MD, Žižak Ž, Savić V. Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry. 2019;2019(29):4701-4709.
doi:10.1002/ejoc.201900672 .

Jovanović, Predrag, Petković, Miloš, Simić, Milena, Jovanović, Miloš, Tasić, Gordana, Crnogorac, Marija Dj., Žižak, Željko, Savić, Vladimir, "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals" in European Journal of Organic Chemistry, 2019, no. 29 (2019):4701-4709,
https://doi.org/10.1002/ejoc.201900672 . .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Radivojević, Jelena
AU  - O'Connor, Kevin
AU  - Blagojević, Stevan
AU  - Begović, Biljana
AU  - Lukić, Vera
AU  - Nikodinović-Runić, Jasmina
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3335
AB  - Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.
PB  - Academic Press Inc Elsevier Science, San Diego
T2  - Bioorganic Chemistry
T1  - Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans
VL  - 87
SP  - 209
EP  - 217
DO  - 10.1016/j.bioorg.2019.03.023
ER  - 

@article{
author = "Jovanović, Miloš and Radivojević, Jelena and O'Connor, Kevin and Blagojević, Stevan and Begović, Biljana and Lukić, Vera and Nikodinović-Runić, Jasmina and Savić, Vladimir",
year = "2019",
abstract = "Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.",
publisher = "Academic Press Inc Elsevier Science, San Diego",
journal = "Bioorganic Chemistry",
title = "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans",
volume = "87",
pages = "209-217",
doi = "10.1016/j.bioorg.2019.03.023"
}

Jovanović, M., Radivojević, J., O'Connor, K., Blagojević, S., Begović, B., Lukić, V., Nikodinović-Runić, J.,& Savić, V.. (2019). Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans. in Bioorganic Chemistry
Academic Press Inc Elsevier Science, San Diego., 87, 209-217.
https://doi.org/10.1016/j.bioorg.2019.03.023

Jovanović M, Radivojević J, O'Connor K, Blagojević S, Begović B, Lukić V, Nikodinović-Runić J, Savić V. Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans. in Bioorganic Chemistry. 2019;87:209-217.
doi:10.1016/j.bioorg.2019.03.023 .

Jovanović, Miloš, Radivojević, Jelena, O'Connor, Kevin, Blagojević, Stevan, Begović, Biljana, Lukić, Vera, Nikodinović-Runić, Jasmina, Savić, Vladimir, "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans" in Bioorganic Chemistry, 87 (2019):209-217,
https://doi.org/10.1016/j.bioorg.2019.03.023 . .

TY  - CONF
AU  - Jovanović, Predrag
AU  - Obradović, Dragiša
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Jovanović, Miloš
AU  - Petković, Miloš
AU  - Savić, Vladimir
PY  - 2018
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5392
AB  - U ovoj studiji prikazana je reakciona sekvenca koja omogućuje dobijanje visoko
funkcionalizovanih ketona polazeći iz monosaharidnih derivata. Primenom Hekove reakcije1
na glikale i naknadnim otvaranjem dihidropiranskog prstena u prisustvu bor-trifluorida
dobijaju se hiralni polifunkcionalizovani ketoni koji mogu biti korisna polazna jedinjenja u
sintezi složenih molekula.
AB  - In this report we describe the reaction sequence for the synthesis of highly functionalised
ketones, starting from monosaccharide derivatives. Heck reaction is utilised to derivatise
glycals followed by dihydropyran ring opening in the presence of boron trifluoride diethyl
etherate. This gives access to polyfunctionalized ketones which can be useful starting
compounds in the synthesis of complex molecules.
PB  - Srpsko hemijsko društvo, Beograd
C3  - 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija
T1  - Od monosaharida do polifunkcionalizovanih ketona
T1  - From monosaharids to polyfunctionalised ketones
SP  - 89
EP  - 89
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5392
ER  - 

@conference{
author = "Jovanović, Predrag and Obradović, Dragiša and Tasić, Gordana and Simić, Milena and Jovanović, Miloš and Petković, Miloš and Savić, Vladimir",
year = "2018",
abstract = "U ovoj studiji prikazana je reakciona sekvenca koja omogućuje dobijanje visoko
funkcionalizovanih ketona polazeći iz monosaharidnih derivata. Primenom Hekove reakcije1
na glikale i naknadnim otvaranjem dihidropiranskog prstena u prisustvu bor-trifluorida
dobijaju se hiralni polifunkcionalizovani ketoni koji mogu biti korisna polazna jedinjenja u
sintezi složenih molekula., In this report we describe the reaction sequence for the synthesis of highly functionalised
ketones, starting from monosaccharide derivatives. Heck reaction is utilised to derivatise
glycals followed by dihydropyran ring opening in the presence of boron trifluoride diethyl
etherate. This gives access to polyfunctionalized ketones which can be useful starting
compounds in the synthesis of complex molecules.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija",
title = "Od monosaharida do polifunkcionalizovanih ketona, From monosaharids to polyfunctionalised ketones",
pages = "89-89",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5392"
}

Jovanović, P., Obradović, D., Tasić, G., Simić, M., Jovanović, M., Petković, M.,& Savić, V.. (2018). Od monosaharida do polifunkcionalizovanih ketona. in 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija
Srpsko hemijsko društvo, Beograd., 89-89.
https://hdl.handle.net/21.15107/rcub_farfar_5392

Jovanović P, Obradović D, Tasić G, Simić M, Jovanović M, Petković M, Savić V. Od monosaharida do polifunkcionalizovanih ketona. in 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija. 2018;:89-89.
https://hdl.handle.net/21.15107/rcub_farfar_5392 .

Jovanović, Predrag, Obradović, Dragiša, Tasić, Gordana, Simić, Milena, Jovanović, Miloš, Petković, Miloš, Savić, Vladimir, "Od monosaharida do polifunkcionalizovanih ketona" in 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija (2018):89-89,
https://hdl.handle.net/21.15107/rcub_farfar_5392 .

TY  - JOUR
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Savić, Vladimir
PY  - 2018
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3040
AB  - A facile synthetic route has been developed for the preparation of pyrrolizinone derivatives employing N-allyl imides as starting materials. The nucleophilic addition of a vinyl Grignard reagent/RCM/elimination sequence afforded pyrrolizinones in good yields and has been applied for the preparation of naturally occurring quinolactacide and marinamide.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - Preparation of pyrrolizinone derivatives via sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide
VL  - 16
IS  - 12
SP  - 2125
EP  - 2133
DO  - 10.1039/c8ob00260f
ER  - 

@article{
author = "Simić, Milena and Tasić, Gordana and Jovanović, Predrag and Petković, Miloš and Savić, Vladimir",
year = "2018",
abstract = "A facile synthetic route has been developed for the preparation of pyrrolizinone derivatives employing N-allyl imides as starting materials. The nucleophilic addition of a vinyl Grignard reagent/RCM/elimination sequence afforded pyrrolizinones in good yields and has been applied for the preparation of naturally occurring quinolactacide and marinamide.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "Preparation of pyrrolizinone derivatives via sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide",
volume = "16",
number = "12",
pages = "2125-2133",
doi = "10.1039/c8ob00260f"
}

Simić, M., Tasić, G., Jovanović, P., Petković, M.,& Savić, V.. (2018). Preparation of pyrrolizinone derivatives via sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 16(12), 2125-2133.
https://doi.org/10.1039/c8ob00260f

Simić M, Tasić G, Jovanović P, Petković M, Savić V. Preparation of pyrrolizinone derivatives via sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide. in Organic & Biomolecular Chemistry. 2018;16(12):2125-2133.
doi:10.1039/c8ob00260f .

Simić, Milena, Tasić, Gordana, Jovanović, Predrag, Petković, Miloš, Savić, Vladimir, "Preparation of pyrrolizinone derivatives via sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide" in Organic & Biomolecular Chemistry, 16, no. 12 (2018):2125-2133,
https://doi.org/10.1039/c8ob00260f . .

TY  - JOUR
AU  - Đukanović, Dimitrije
AU  - Petković, Miloš
AU  - Simić, Milena
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Savić, Vladimir
PY  - 2018
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3037
AB  - A one-pot, domino process was developed as an alternative approach for the preparation of 2-unsubstituted imidazolones. The methodology utilizes readily accessible bisamides, which upon a dehydration/-cyclisation sequence produced imidazolones in good yields. The transformation relies on the compatibility of the dehydrating agent and base, and the reaction conditions tolerate various functional groups.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot, domino dehydration/base promoted cyclisation process
VL  - 59
IS  - 10
SP  - 914
EP  - 917
DO  - 10.1016/j.tetlet.2018.01.074
ER  - 

@article{
author = "Đukanović, Dimitrije and Petković, Miloš and Simić, Milena and Jovanović, Predrag and Tasić, Gordana and Savić, Vladimir",
year = "2018",
abstract = "A one-pot, domino process was developed as an alternative approach for the preparation of 2-unsubstituted imidazolones. The methodology utilizes readily accessible bisamides, which upon a dehydration/-cyclisation sequence produced imidazolones in good yields. The transformation relies on the compatibility of the dehydrating agent and base, and the reaction conditions tolerate various functional groups.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot, domino dehydration/base promoted cyclisation process",
volume = "59",
number = "10",
pages = "914-917",
doi = "10.1016/j.tetlet.2018.01.074"
}

Đukanović, D., Petković, M., Simić, M., Jovanović, P., Tasić, G.,& Savić, V.. (2018). Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot, domino dehydration/base promoted cyclisation process. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 59(10), 914-917.
https://doi.org/10.1016/j.tetlet.2018.01.074

Đukanović D, Petković M, Simić M, Jovanović P, Tasić G, Savić V. Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot, domino dehydration/base promoted cyclisation process. in Tetrahedron-Asymmetry. 2018;59(10):914-917.
doi:10.1016/j.tetlet.2018.01.074 .

Đukanović, Dimitrije, Petković, Miloš, Simić, Milena, Jovanović, Predrag, Tasić, Gordana, Savić, Vladimir, "Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot, domino dehydration/base promoted cyclisation process" in Tetrahedron-Asymmetry, 59, no. 10 (2018):914-917,
https://doi.org/10.1016/j.tetlet.2018.01.074 . .

TY  - CONF
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Savić, Vladimir
PY  - 2017
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5382
AB  - Imidazoloni 2 pokazuju različita zanimljiva svojstva u biologiji, farmakologiji i fotohemiji.1,2
Razvijena je blaga i efikasna intramolekulska ciklizacija diamidnih jedinjenja 1, dobijenih Ugijevom
reakcijom, koja dovodi do nastanka derivata imidazolona. Ovom transformacijom se dobijaju
proizvodi u dobrim prinosima u kratkom reakcionom vremenu
AB  - Imidazolones 2 exhibit a variety of interesting properties in biology, pharmacology and
photochemistry.1,2 Mild and efficient intramolecular cyclization of diamide compounds, obtained by
the Ugi reaction, leading to imidazolone derivatives has been developed. The transformation affords
the products in good yields in a short reaction time.
PB  - Srpsko hemijsko društvo, Beograd
C3  - 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija
T1  - Sinteza derivata imidazolona promovisana pomoću 1,8-diazabiciklo[5.4.0]undec-7-ena (DBU)
T1  - Imidazolone derivatives synthesis promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)
SP  - 88
EP  - 88
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5382
ER  - 

@conference{
author = "Petković, Miloš and Jovanović, Predrag and Simić, Milena and Tasić, Gordana and Savić, Vladimir",
year = "2017",
abstract = "Imidazoloni 2 pokazuju različita zanimljiva svojstva u biologiji, farmakologiji i fotohemiji.1,2
Razvijena je blaga i efikasna intramolekulska ciklizacija diamidnih jedinjenja 1, dobijenih Ugijevom
reakcijom, koja dovodi do nastanka derivata imidazolona. Ovom transformacijom se dobijaju
proizvodi u dobrim prinosima u kratkom reakcionom vremenu, Imidazolones 2 exhibit a variety of interesting properties in biology, pharmacology and
photochemistry.1,2 Mild and efficient intramolecular cyclization of diamide compounds, obtained by
the Ugi reaction, leading to imidazolone derivatives has been developed. The transformation affords
the products in good yields in a short reaction time.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija",
title = "Sinteza derivata imidazolona promovisana pomoću 1,8-diazabiciklo[5.4.0]undec-7-ena (DBU), Imidazolone derivatives synthesis promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)",
pages = "88-88",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5382"
}

Petković, M., Jovanović, P., Simić, M., Tasić, G.,& Savić, V.. (2017). Sinteza derivata imidazolona promovisana pomoću 1,8-diazabiciklo[5.4.0]undec-7-ena (DBU). in 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija
Srpsko hemijsko društvo, Beograd., 88-88.
https://hdl.handle.net/21.15107/rcub_farfar_5382

Petković M, Jovanović P, Simić M, Tasić G, Savić V. Sinteza derivata imidazolona promovisana pomoću 1,8-diazabiciklo[5.4.0]undec-7-ena (DBU). in 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija. 2017;:88-88.
https://hdl.handle.net/21.15107/rcub_farfar_5382 .

Petković, Miloš, Jovanović, Predrag, Simić, Milena, Tasić, Gordana, Savić, Vladimir, "Sinteza derivata imidazolona promovisana pomoću 1,8-diazabiciklo[5.4.0]undec-7-ena (DBU)" in 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija (2017):88-88,
https://hdl.handle.net/21.15107/rcub_farfar_5382 .

TY  - CONF
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Savić, Vladimir
PY  - 2017
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5383
AB  - Kondenzovani piroli ulaze u sastav mnogih prirodnih proizvoda i biološki aktivnih jedinjenja.1,2 U
ovoj studiji prikazana je reakciona sekvenca koja omogućuje dobijanje različitih pirolizinona,
kondenzovanih derivata pirola i ciklopentanona, primenom hemije organometala. Adicijom
vinilmagnezijum bromida na N-alilovane imide, zatvaranjem prstena olefinskom metatezom koje je
praćeno dehidratacijom i aromatizacijom moguće je dobiti različite pirolizinone u dobrom prinosu
AB  - Pyrrole based fused heterocyclic compounds are widespread in various natural products and
bioactive compounds. In this report we describe the reaction sequence for synthesis of various
pyrrolizinone derivatives, utilising the chemistry of organometallic compounds. Addition of
vinylmagnesium bromide to N-allyl imides, followed by RCM reaction, dehydration and
aromatisation, pyrrolizinones were obtained in good yields.
PB  - Srpsko hemijsko društvo, Beograd
C3  - 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija
T1  - Sekvencijalne reakcije organometala u sintezi kondenzovanih derivata pirola
T1  - Sequential reaction of organometallics in synthesis of fused pyrrole derivatives
SP  - 87
EP  - 87
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5383
ER  - 

@conference{
author = "Simić, Milena and Tasić, Gordana and Petković, Miloš and Jovanović, Predrag and Savić, Vladimir",
year = "2017",
abstract = "Kondenzovani piroli ulaze u sastav mnogih prirodnih proizvoda i biološki aktivnih jedinjenja.1,2 U
ovoj studiji prikazana je reakciona sekvenca koja omogućuje dobijanje različitih pirolizinona,
kondenzovanih derivata pirola i ciklopentanona, primenom hemije organometala. Adicijom
vinilmagnezijum bromida na N-alilovane imide, zatvaranjem prstena olefinskom metatezom koje je
praćeno dehidratacijom i aromatizacijom moguće je dobiti različite pirolizinone u dobrom prinosu, Pyrrole based fused heterocyclic compounds are widespread in various natural products and
bioactive compounds. In this report we describe the reaction sequence for synthesis of various
pyrrolizinone derivatives, utilising the chemistry of organometallic compounds. Addition of
vinylmagnesium bromide to N-allyl imides, followed by RCM reaction, dehydration and
aromatisation, pyrrolizinones were obtained in good yields.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija",
title = "Sekvencijalne reakcije organometala u sintezi kondenzovanih derivata pirola, Sequential reaction of organometallics in synthesis of fused pyrrole derivatives",
pages = "87-87",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5383"
}

Simić, M., Tasić, G., Petković, M., Jovanović, P.,& Savić, V.. (2017). Sekvencijalne reakcije organometala u sintezi kondenzovanih derivata pirola. in 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija
Srpsko hemijsko društvo, Beograd., 87-87.
https://hdl.handle.net/21.15107/rcub_farfar_5383

Simić M, Tasić G, Petković M, Jovanović P, Savić V. Sekvencijalne reakcije organometala u sintezi kondenzovanih derivata pirola. in 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija. 2017;:87-87.
https://hdl.handle.net/21.15107/rcub_farfar_5383 .

Simić, Milena, Tasić, Gordana, Petković, Miloš, Jovanović, Predrag, Savić, Vladimir, "Sekvencijalne reakcije organometala u sintezi kondenzovanih derivata pirola" in 54. Savetovanje Srpskog hemijskog društva. 5. Konferencija mladih hemičara Srbije. Kratki izvodi, Septembar 29 i 30, 2017, Beograd, Srbija (2017):87-87,
https://hdl.handle.net/21.15107/rcub_farfar_5383 .

TY  - JOUR
AU  - Simić, Milena
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Savić, Vladimir
PY  - 2017
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2842
AB  - Pd-catalysed arylation-acetoxylation cascade, a previously reported methodology, was applied in the functionalisation of unsymmetrical dienes. Both explored classes of compounds, isoquinoline and ss-carboline-derived dienes, afforded single regioisomers. Although further improvements of the process are necessary, primarily due to lower yields, the described functionalisation of the studied compounds might be useful in the synthesis of emetine and related naturally occurring compounds.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of substituted allyl acetates from heterocyclic dienes by a Pd-promoted arylation-acetoxylation cascade
VL  - 82
IS  - 12
SP  - 1335
EP  - 1341
DO  - 10.2298/JSC170317046S
ER  - 

@article{
author = "Simić, Milena and Petković, Miloš and Jovanović, Predrag and Tasić, Gordana and Savić, Vladimir",
year = "2017",
abstract = "Pd-catalysed arylation-acetoxylation cascade, a previously reported methodology, was applied in the functionalisation of unsymmetrical dienes. Both explored classes of compounds, isoquinoline and ss-carboline-derived dienes, afforded single regioisomers. Although further improvements of the process are necessary, primarily due to lower yields, the described functionalisation of the studied compounds might be useful in the synthesis of emetine and related naturally occurring compounds.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of substituted allyl acetates from heterocyclic dienes by a Pd-promoted arylation-acetoxylation cascade",
volume = "82",
number = "12",
pages = "1335-1341",
doi = "10.2298/JSC170317046S"
}

Simić, M., Petković, M., Jovanović, P., Tasić, G.,& Savić, V.. (2017). Synthesis of substituted allyl acetates from heterocyclic dienes by a Pd-promoted arylation-acetoxylation cascade. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 82(12), 1335-1341.
https://doi.org/10.2298/JSC170317046S

Simić M, Petković M, Jovanović P, Tasić G, Savić V. Synthesis of substituted allyl acetates from heterocyclic dienes by a Pd-promoted arylation-acetoxylation cascade. in Journal of the Serbian Chemical Society. 2017;82(12):1335-1341.
doi:10.2298/JSC170317046S .

Simić, Milena, Petković, Miloš, Jovanović, Predrag, Tasić, Gordana, Savić, Vladimir, "Synthesis of substituted allyl acetates from heterocyclic dienes by a Pd-promoted arylation-acetoxylation cascade" in Journal of the Serbian Chemical Society, 82, no. 12 (2017):1335-1341,
https://doi.org/10.2298/JSC170317046S . .

TY  - JOUR
AU  - Simić, Milena
AU  - Damjanović, Ana B.
AU  - Kalinić, Marko
AU  - Tasić, Gordana
AU  - Erić, Slavica
AU  - Antić-Stanković, Jelena
AU  - Savić, Vladimir
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2606
AB  - A novel and efficient synthetic route was developed for the preparation of protoberberine derivatives. A methodology, designed primarily to control the substitution patterns on the terminal rings, was used to access a small array of these compounds. An initial biological profiling suggested an anticancer potential of the synthesised derivatives, while structure-based target fishing identified their potential targets and established a rational basis for further structural modifications. Although the activities need further improvement, the study demonstrated that the described approach may be useful in the discovery of novel lead compounds.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, cytotoxicity and computational study of novel protoberberine derivatives
VL  - 81
IS  - 2
SP  - 103
EP  - 123
DO  - 10.2298/JSC150525090S
ER  - 

@article{
author = "Simić, Milena and Damjanović, Ana B. and Kalinić, Marko and Tasić, Gordana and Erić, Slavica and Antić-Stanković, Jelena and Savić, Vladimir",
year = "2016",
abstract = "A novel and efficient synthetic route was developed for the preparation of protoberberine derivatives. A methodology, designed primarily to control the substitution patterns on the terminal rings, was used to access a small array of these compounds. An initial biological profiling suggested an anticancer potential of the synthesised derivatives, while structure-based target fishing identified their potential targets and established a rational basis for further structural modifications. Although the activities need further improvement, the study demonstrated that the described approach may be useful in the discovery of novel lead compounds.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, cytotoxicity and computational study of novel protoberberine derivatives",
volume = "81",
number = "2",
pages = "103-123",
doi = "10.2298/JSC150525090S"
}

Simić, M., Damjanović, A. B., Kalinić, M., Tasić, G., Erić, S., Antić-Stanković, J.,& Savić, V.. (2016). Synthesis, cytotoxicity and computational study of novel protoberberine derivatives. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 81(2), 103-123.
https://doi.org/10.2298/JSC150525090S

Simić M, Damjanović AB, Kalinić M, Tasić G, Erić S, Antić-Stanković J, Savić V. Synthesis, cytotoxicity and computational study of novel protoberberine derivatives. in Journal of the Serbian Chemical Society. 2016;81(2):103-123.
doi:10.2298/JSC150525090S .

Simić, Milena, Damjanović, Ana B., Kalinić, Marko, Tasić, Gordana, Erić, Slavica, Antić-Stanković, Jelena, Savić, Vladimir, "Synthesis, cytotoxicity and computational study of novel protoberberine derivatives" in Journal of the Serbian Chemical Society, 81, no. 2 (2016):103-123,
https://doi.org/10.2298/JSC150525090S . .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Simić, Milena
AU  - Ivković, Branka
AU  - Savić, Vladimir
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2647
AB  - A novel thiourea organocatalyst was rationally designed by altering a typical H-bonding pattern of thiourea derivatives and utilising the potential of the 3,5-bis(trifluoromethyl) phenyl motif to participate in the H-bond formation. This unique catalyst afforded the products of the alpha-amination and Michael reaction in excellent yields and with a high level of stereoselectivity. Although additional studies are necessary to establish the full potential of the catalyst and to broaden its application further, the presented results may indicate alternative routes for further exploration of the thiourea class of organocatalysts.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - A novel thiourea type organocatalyst possessing a single NH functionality
VL  - 14
IS  - 28
SP  - 6712
EP  - 6719
DO  - 10.1039/c6ob00387g
ER  - 

@article{
author = "Jovanović, Predrag and Petković, Miloš and Simić, Milena and Ivković, Branka and Savić, Vladimir",
year = "2016",
abstract = "A novel thiourea organocatalyst was rationally designed by altering a typical H-bonding pattern of thiourea derivatives and utilising the potential of the 3,5-bis(trifluoromethyl) phenyl motif to participate in the H-bond formation. This unique catalyst afforded the products of the alpha-amination and Michael reaction in excellent yields and with a high level of stereoselectivity. Although additional studies are necessary to establish the full potential of the catalyst and to broaden its application further, the presented results may indicate alternative routes for further exploration of the thiourea class of organocatalysts.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "A novel thiourea type organocatalyst possessing a single NH functionality",
volume = "14",
number = "28",
pages = "6712-6719",
doi = "10.1039/c6ob00387g"
}

Jovanović, P., Petković, M., Simić, M., Ivković, B.,& Savić, V.. (2016). A novel thiourea type organocatalyst possessing a single NH functionality. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 14(28), 6712-6719.
https://doi.org/10.1039/c6ob00387g

Jovanović P, Petković M, Simić M, Ivković B, Savić V. A novel thiourea type organocatalyst possessing a single NH functionality. in Organic & Biomolecular Chemistry. 2016;14(28):6712-6719.
doi:10.1039/c6ob00387g .

Jovanović, Predrag, Petković, Miloš, Simić, Milena, Ivković, Branka, Savić, Vladimir, "A novel thiourea type organocatalyst possessing a single NH functionality" in Organic & Biomolecular Chemistry, 14, no. 28 (2016):6712-6719,
https://doi.org/10.1039/c6ob00387g . .

TY  - JOUR
AU  - Simić, Milena
AU  - Paunović, Nikola
AU  - Borić, Ivan
AU  - Ranđelović, Jelena
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Pekmezović, Marina
AU  - Savić, Vladimir
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2580
AB  - A series of novel 3-substituted isocoumarins was prepared via Pd-catalysed coupling processes and screened in vitro for antifungal activity against Candida species. The study revealed antifungal potential of isocoumarins possessing the azole substituents, which, in some cases, showed biological properties equal to those of clinically used voriconazole. Selected compounds were also screened against voriconazole resistant Candida krusei 6258 and a clinical isolate Candida parapsilosis CA-27. Although the activity against these targets needs to be improved further, the results emphasise additional potential of this new class of antifungal compounds.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies
VL  - 26
IS  - 1
SP  - 235
EP  - 239
DO  - 10.1016/j.bmcl.2015.08.086
ER  - 

@article{
author = "Simić, Milena and Paunović, Nikola and Borić, Ivan and Ranđelović, Jelena and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Pekmezović, Marina and Savić, Vladimir",
year = "2016",
abstract = "A series of novel 3-substituted isocoumarins was prepared via Pd-catalysed coupling processes and screened in vitro for antifungal activity against Candida species. The study revealed antifungal potential of isocoumarins possessing the azole substituents, which, in some cases, showed biological properties equal to those of clinically used voriconazole. Selected compounds were also screened against voriconazole resistant Candida krusei 6258 and a clinical isolate Candida parapsilosis CA-27. Although the activity against these targets needs to be improved further, the results emphasise additional potential of this new class of antifungal compounds.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies",
volume = "26",
number = "1",
pages = "235-239",
doi = "10.1016/j.bmcl.2015.08.086"
}

Simić, M., Paunović, N., Borić, I., Ranđelović, J., Vojnović, S., Nikodinović-Runić, J., Pekmezović, M.,& Savić, V.. (2016). Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies. in Bioorganic & Medicinal Chemistry Letters
Pergamon-Elsevier Science Ltd, Oxford., 26(1), 235-239.
https://doi.org/10.1016/j.bmcl.2015.08.086

Simić M, Paunović N, Borić I, Ranđelović J, Vojnović S, Nikodinović-Runić J, Pekmezović M, Savić V. Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies. in Bioorganic & Medicinal Chemistry Letters. 2016;26(1):235-239.
doi:10.1016/j.bmcl.2015.08.086 .

Simić, Milena, Paunović, Nikola, Borić, Ivan, Ranđelović, Jelena, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Pekmezović, Marina, Savić, Vladimir, "Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies" in Bioorganic & Medicinal Chemistry Letters, 26, no. 1 (2016):235-239,
https://doi.org/10.1016/j.bmcl.2015.08.086 . .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Ivković, Branka
AU  - Savić, Vladimir
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2723
AB  - Structural variations of the heterocyclic ring of the recently introduced pyrrolidine derived thiourea organocatalysts have been studied. The results showed that the stereoselectivity is highly dependent on the substitution pattern reaching a moderate level, while the yields were generally less influenced by the structural changes. The outlined results may be helpful in further exploration of the thiourea catalyst represented by structure II.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Therapeutic Advances in Drug Safety
T1  - Pyrrolidine derived thioureas as organocatalysts in the Michael reaction of vinyl sulfone. Structure-stereoselectivity study
VL  - 27
IS  - 19
SP  - 990
EP  - 997
DO  - 10.1016/j.tetasy.2016.08.004
ER  - 

@article{
author = "Jovanović, Predrag and Petković, Miloš and Ivković, Branka and Savić, Vladimir",
year = "2016",
abstract = "Structural variations of the heterocyclic ring of the recently introduced pyrrolidine derived thiourea organocatalysts have been studied. The results showed that the stereoselectivity is highly dependent on the substitution pattern reaching a moderate level, while the yields were generally less influenced by the structural changes. The outlined results may be helpful in further exploration of the thiourea catalyst represented by structure II.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Therapeutic Advances in Drug Safety",
title = "Pyrrolidine derived thioureas as organocatalysts in the Michael reaction of vinyl sulfone. Structure-stereoselectivity study",
volume = "27",
number = "19",
pages = "990-997",
doi = "10.1016/j.tetasy.2016.08.004"
}

Jovanović, P., Petković, M., Ivković, B.,& Savić, V.. (2016). Pyrrolidine derived thioureas as organocatalysts in the Michael reaction of vinyl sulfone. Structure-stereoselectivity study. in Therapeutic Advances in Drug Safety
Pergamon-Elsevier Science Ltd, Oxford., 27(19), 990-997.
https://doi.org/10.1016/j.tetasy.2016.08.004

Jovanović P, Petković M, Ivković B, Savić V. Pyrrolidine derived thioureas as organocatalysts in the Michael reaction of vinyl sulfone. Structure-stereoselectivity study. in Therapeutic Advances in Drug Safety. 2016;27(19):990-997.
doi:10.1016/j.tetasy.2016.08.004 .

Jovanović, Predrag, Petković, Miloš, Ivković, Branka, Savić, Vladimir, "Pyrrolidine derived thioureas as organocatalysts in the Michael reaction of vinyl sulfone. Structure-stereoselectivity study" in Therapeutic Advances in Drug Safety, 27, no. 19 (2016):990-997,
https://doi.org/10.1016/j.tetasy.2016.08.004 . .

TY  - JOUR
AU  - Petković, Miloš
AU  - Nasufović, Veselin
AU  - Đukanović, Dimitrije
AU  - Tokić-Vujošević, Zorana
AU  - Jadranin, Milka
AU  - Matović, Radomir
AU  - Savić, Vladimir
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2603
AB  - Allenamides derived from amino acids participate in the cascade transformations catalyzed by Pd-0 allowing consecutive formation of two five-membered rings. The developed methodology provides an access to annulated indoles which can be transformed to functionalized indoxyl derivatives, retaining a structural motif embedded in several natural products.
PB  - Wiley-VCH Verlag GMBH, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives
IS  - 7
SP  - 1279
EP  - 1282
DO  - 10.1002/ejoc.201600067
ER  - 

@article{
author = "Petković, Miloš and Nasufović, Veselin and Đukanović, Dimitrije and Tokić-Vujošević, Zorana and Jadranin, Milka and Matović, Radomir and Savić, Vladimir",
year = "2016",
abstract = "Allenamides derived from amino acids participate in the cascade transformations catalyzed by Pd-0 allowing consecutive formation of two five-membered rings. The developed methodology provides an access to annulated indoles which can be transformed to functionalized indoxyl derivatives, retaining a structural motif embedded in several natural products.",
publisher = "Wiley-VCH Verlag GMBH, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives",
number = "7",
pages = "1279-1282",
doi = "10.1002/ejoc.201600067"
}

Petković, M., Nasufović, V., Đukanović, D., Tokić-Vujošević, Z., Jadranin, M., Matović, R.,& Savić, V.. (2016). Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives. in European Journal of Organic Chemistry
Wiley-VCH Verlag GMBH, Weinheim.(7), 1279-1282.
https://doi.org/10.1002/ejoc.201600067

Petković M, Nasufović V, Đukanović D, Tokić-Vujošević Z, Jadranin M, Matović R, Savić V. Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives. in European Journal of Organic Chemistry. 2016;(7):1279-1282.
doi:10.1002/ejoc.201600067 .

Petković, Miloš, Nasufović, Veselin, Đukanović, Dimitrije, Tokić-Vujošević, Zorana, Jadranin, Milka, Matović, Radomir, Savić, Vladimir, "Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives" in European Journal of Organic Chemistry, no. 7 (2016):1279-1282,
https://doi.org/10.1002/ejoc.201600067 . .

TY  - JOUR
AU  - Simić, Milena
AU  - Stanković, Miroslava
AU  - Mandić, Boris M.
AU  - Tešević, Vele
AU  - Savić, Vladimir
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2450
AB  - Cytoprotective compounds such as amifostine play an important role in chemo-and radiotherapy due to their ability to reduce the side effects of these treatments. Our work was initiated with the intention to design, synthesise and test a new class of heterocyclic compounds that would have an antioxidative profile with the potential to be further developed as cytoprotective agents. The design was based on the privileged tetrahydrobenzazepine scaffold found in many natural products with a wide range of biological properties. This structure was further functionalised with moieties known to possess antioxidative features such as tertiary amine and styrene double bond. A series of eight tetrahydrobenzazepine derivatives of isoquinoline, 3,4-dihydro-beta-carboline and pyridine were synthesised employing the Heck reaction as a key transformation. Some of the prepared compounds were tested for their in vitro effects on chromosome aberrations in peripheral human lymphocytes using the cytochalasin-B blocked micronucleus (MN) assay. Three tetrahydrobenzoazepine derivatives showed significant cytoprotective properties, comparable or even better to those of the radioprotective agent amifostine.
PB  - Wiley-VCH Verlag GMBH, Weinheim
T2  - Archiv der Pharmazie
T1  - Synthesis of Novel Tetrahydrobenzazepine Derivatives and Their Cytoprotective Effect on Human Lymphocytes
VL  - 348
IS  - 2
SP  - 100
EP  - 112
DO  - 10.1002/ardp.201400350
ER  - 

@article{
author = "Simić, Milena and Stanković, Miroslava and Mandić, Boris M. and Tešević, Vele and Savić, Vladimir",
year = "2015",
abstract = "Cytoprotective compounds such as amifostine play an important role in chemo-and radiotherapy due to their ability to reduce the side effects of these treatments. Our work was initiated with the intention to design, synthesise and test a new class of heterocyclic compounds that would have an antioxidative profile with the potential to be further developed as cytoprotective agents. The design was based on the privileged tetrahydrobenzazepine scaffold found in many natural products with a wide range of biological properties. This structure was further functionalised with moieties known to possess antioxidative features such as tertiary amine and styrene double bond. A series of eight tetrahydrobenzazepine derivatives of isoquinoline, 3,4-dihydro-beta-carboline and pyridine were synthesised employing the Heck reaction as a key transformation. Some of the prepared compounds were tested for their in vitro effects on chromosome aberrations in peripheral human lymphocytes using the cytochalasin-B blocked micronucleus (MN) assay. Three tetrahydrobenzoazepine derivatives showed significant cytoprotective properties, comparable or even better to those of the radioprotective agent amifostine.",
publisher = "Wiley-VCH Verlag GMBH, Weinheim",
journal = "Archiv der Pharmazie",
title = "Synthesis of Novel Tetrahydrobenzazepine Derivatives and Their Cytoprotective Effect on Human Lymphocytes",
volume = "348",
number = "2",
pages = "100-112",
doi = "10.1002/ardp.201400350"
}

Simić, M., Stanković, M., Mandić, B. M., Tešević, V.,& Savić, V.. (2015). Synthesis of Novel Tetrahydrobenzazepine Derivatives and Their Cytoprotective Effect on Human Lymphocytes. in Archiv der Pharmazie
Wiley-VCH Verlag GMBH, Weinheim., 348(2), 100-112.
https://doi.org/10.1002/ardp.201400350

Simić M, Stanković M, Mandić BM, Tešević V, Savić V. Synthesis of Novel Tetrahydrobenzazepine Derivatives and Their Cytoprotective Effect on Human Lymphocytes. in Archiv der Pharmazie. 2015;348(2):100-112.
doi:10.1002/ardp.201400350 .

Simić, Milena, Stanković, Miroslava, Mandić, Boris M., Tešević, Vele, Savić, Vladimir, "Synthesis of Novel Tetrahydrobenzazepine Derivatives and Their Cytoprotective Effect on Human Lymphocytes" in Archiv der Pharmazie, 348, no. 2 (2015):100-112,
https://doi.org/10.1002/ardp.201400350 . .

TY  - JOUR
AU  - Erić, Slavica
AU  - Kalinić, Marko
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2515
AB  - P-glycoprotein (Pgp) is a transmembrane transporter which can, by transporting structurally diverse compounds, influence the absorption, distribution and efficacy of a number of drugs. Pgp overexpression in cells is a major contributing factor to the development of drug resistance. For these reasons, potential for compound efflux by Pgp should be assessed early on in the drug discovery process, preferably even prior to compound synthesis. To meet this demand, numerous computational models have been developed during the past decade, capable of predicting Pgp-mediated transport based solely on chemical structures. This paper summarizes the various approaches that have been used for model development, discusses their advantages and disadvantages and focuses on key factors that influence model reliability. The promiscuous nature of the transport can be seen as a major challenge for most computational chemistry methods. Nevertheless, the attained level of accuracy of literature models suggests that they can be useful in the drug discovery setting. Greater availability of experimental data and integration of predictions made by different modeling methods has the potential to further improve the reliability of computational predictions.
AB  - P-glikoprotein (Pgp) je transmembranski transporter koji, transportujući strukturno raznovrsne lekove iz unutrašnjosti ćelije u ekstracelularnu sredinu, može uticati na resorpciju, distribuciju i efikasnost većeg broja lekova. Prekomerna ekspresija Pgp-a u ćelijama predstavlja jedan od mehanizama razvoja rezistencije na lekove. Iz ovih razloga, potrebno je u ranoj fazi otkrića leka predvideti da li je potencijalni lek supstrat za Pgp, idealno i pre same sinteze. U tu svrhu, tokom poslednje decenije razvijen je veliki broj računarskih modela koji omogućavaju predviđanje transporta posredstvom Pgp-a samo na osnovu hemijske strukture. U ovom radu prikazan je pregled različitih pristupa koji su korišćeni u razvoju modela, razmotrene su njihove prednosti i nedostaci, kao i faktori koji u najvećoj meri utiču na pouzdanost predviđanja. Polispecifičnost ovog transportera predstavlja značajan izazov za većinu metoda računarske hemije. Ipak, dostignut nivo tačnosti modela koji su prikazani u litearaturi ukazuje na činjenicu da oni mogu doprineti racionalizaciji procesa dizajniranja novih lekova. Šira dostupnost eksperimentalnih podataka, kao i kombinovanje različitih pristupa modelovanju transporta, mogu dodatno unaprediti postojeće modele.
PB  - Savez farmaceutskih udruženja Srbije, Beograd
T2  - Arhiv za farmaciju
T1  - Computational models for predicting drug transport mediated by P-glycoprotein
T1  - Računarski modeli za predviđanje transporta lekova posredovanog P-glikoproteinom
VL  - 65
IS  - 2
SP  - 89
EP  - 114
DO  - 10.5937/arhfarm1502089E
ER  - 

@article{
author = "Erić, Slavica and Kalinić, Marko",
year = "2015",
abstract = "P-glycoprotein (Pgp) is a transmembrane transporter which can, by transporting structurally diverse compounds, influence the absorption, distribution and efficacy of a number of drugs. Pgp overexpression in cells is a major contributing factor to the development of drug resistance. For these reasons, potential for compound efflux by Pgp should be assessed early on in the drug discovery process, preferably even prior to compound synthesis. To meet this demand, numerous computational models have been developed during the past decade, capable of predicting Pgp-mediated transport based solely on chemical structures. This paper summarizes the various approaches that have been used for model development, discusses their advantages and disadvantages and focuses on key factors that influence model reliability. The promiscuous nature of the transport can be seen as a major challenge for most computational chemistry methods. Nevertheless, the attained level of accuracy of literature models suggests that they can be useful in the drug discovery setting. Greater availability of experimental data and integration of predictions made by different modeling methods has the potential to further improve the reliability of computational predictions., P-glikoprotein (Pgp) je transmembranski transporter koji, transportujući strukturno raznovrsne lekove iz unutrašnjosti ćelije u ekstracelularnu sredinu, može uticati na resorpciju, distribuciju i efikasnost većeg broja lekova. Prekomerna ekspresija Pgp-a u ćelijama predstavlja jedan od mehanizama razvoja rezistencije na lekove. Iz ovih razloga, potrebno je u ranoj fazi otkrića leka predvideti da li je potencijalni lek supstrat za Pgp, idealno i pre same sinteze. U tu svrhu, tokom poslednje decenije razvijen je veliki broj računarskih modela koji omogućavaju predviđanje transporta posredstvom Pgp-a samo na osnovu hemijske strukture. U ovom radu prikazan je pregled različitih pristupa koji su korišćeni u razvoju modela, razmotrene su njihove prednosti i nedostaci, kao i faktori koji u najvećoj meri utiču na pouzdanost predviđanja. Polispecifičnost ovog transportera predstavlja značajan izazov za većinu metoda računarske hemije. Ipak, dostignut nivo tačnosti modela koji su prikazani u litearaturi ukazuje na činjenicu da oni mogu doprineti racionalizaciji procesa dizajniranja novih lekova. Šira dostupnost eksperimentalnih podataka, kao i kombinovanje različitih pristupa modelovanju transporta, mogu dodatno unaprediti postojeće modele.",
publisher = "Savez farmaceutskih udruženja Srbije, Beograd",
journal = "Arhiv za farmaciju",
title = "Computational models for predicting drug transport mediated by P-glycoprotein, Računarski modeli za predviđanje transporta lekova posredovanog P-glikoproteinom",
volume = "65",
number = "2",
pages = "89-114",
doi = "10.5937/arhfarm1502089E"
}

Erić, S.,& Kalinić, M.. (2015). Computational models for predicting drug transport mediated by P-glycoprotein. in Arhiv za farmaciju
Savez farmaceutskih udruženja Srbije, Beograd., 65(2), 89-114.
https://doi.org/10.5937/arhfarm1502089E

Erić S, Kalinić M. Computational models for predicting drug transport mediated by P-glycoprotein. in Arhiv za farmaciju. 2015;65(2):89-114.
doi:10.5937/arhfarm1502089E .

Erić, Slavica, Kalinić, Marko, "Computational models for predicting drug transport mediated by P-glycoprotein" in Arhiv za farmaciju, 65, no. 2 (2015):89-114,
https://doi.org/10.5937/arhfarm1502089E . .

TY  - JOUR
AU  - Tasić, Gordana
AU  - Maslak, Veselin
AU  - Husinec, Suren
AU  - Todorović, Nina
AU  - Savić, Vladimir
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2375
AB  - The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine
VL  - 56
IS  - 19
SP  - 2529
EP  - 2532
DO  - 10.1016/j.tetlet.2015.03.129
ER  - 

@article{
author = "Tasić, Gordana and Maslak, Veselin and Husinec, Suren and Todorović, Nina and Savić, Vladimir",
year = "2015",
abstract = "The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine",
volume = "56",
number = "19",
pages = "2529-2532",
doi = "10.1016/j.tetlet.2015.03.129"
}

Tasić, G., Maslak, V., Husinec, S., Todorović, N.,& Savić, V.. (2015). Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 56(19), 2529-2532.
https://doi.org/10.1016/j.tetlet.2015.03.129

Tasić G, Maslak V, Husinec S, Todorović N, Savić V. Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry. 2015;56(19):2529-2532.
doi:10.1016/j.tetlet.2015.03.129 .

Tasić, Gordana, Maslak, Veselin, Husinec, Suren, Todorović, Nina, Savić, Vladimir, "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine" in Tetrahedron-Asymmetry, 56, no. 19 (2015):2529-2532,
https://doi.org/10.1016/j.tetlet.2015.03.129 . .

TY  - JOUR
AU  - Ranđelović, Jelena
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Husinec, Suren
AU  - Savić, Vladimir
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2090
AB  - Cycloaddition reactions of azomethine ylides are the most direct way to synthesise pyrrolidine derivatives. They have been studied for several decades and have become an indispensable tool in synthesis of pyrrolidines and pyrrolidine derived natural products. Amongst many methods for generating azomethine ylides, various processes involving imines derived from amino acid esters have been the most frequently studied. The use of Lewis acids to promote imine-ylide-cycloaddition sequence under mild conditions, in recent years, has led to the development of highly stereoselective metal catalysed methodologies for the preparation of pyrrolidine derivatives. In the last few years, the concept of organocatalysis has been incorporated in cycloaddition reactions of azomethine ylides providing an alternative access to chiral pyrrolidines. Several classes of typical organocatalysts such as prolines, phosphoric acids, thioureas, guanidines and sulphuric acid derivatives have been used for these purposes. Various mechanistic pathways have been proposed, based on either the activation of only one reacting partner, 1,3-dipole (imine) or dipolarophile (alkene), or both of them simultaneously. While the first three classes of organocatalysts appear to afford pyrrolidines, generally, in good yields and with high levels of stereoselectivity, guanidines and sulphuric acid derivatives are less efficient, but also the least studied catalyst group. A whole range of electron deficient dipolarophiles (alkenes) have been used in these cycloaddition processes, while, regarding the dipole precursor imine, aromatic aldimines seem to be more efficient than their aliphatic equivalents. There is no doubt that the recent progress in organocatalytic cycloadditions of azomethine ylides created new possibilities for synthesis of pyrrolidine derivatives and enriched this useful synthetic methodology.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Current Organic Chemistry
T1  - Organocatalysis in Synthesis of Pyrrolidine Derivatives via Cycloaddition Reactions of Azomethine Ylides
VL  - 18
IS  - 9
SP  - 1073
EP  - 1096
DO  - 10.2174/1385272819999140404130229
ER  - 

@article{
author = "Ranđelović, Jelena and Simić, Milena and Tasić, Gordana and Husinec, Suren and Savić, Vladimir",
year = "2014",
abstract = "Cycloaddition reactions of azomethine ylides are the most direct way to synthesise pyrrolidine derivatives. They have been studied for several decades and have become an indispensable tool in synthesis of pyrrolidines and pyrrolidine derived natural products. Amongst many methods for generating azomethine ylides, various processes involving imines derived from amino acid esters have been the most frequently studied. The use of Lewis acids to promote imine-ylide-cycloaddition sequence under mild conditions, in recent years, has led to the development of highly stereoselective metal catalysed methodologies for the preparation of pyrrolidine derivatives. In the last few years, the concept of organocatalysis has been incorporated in cycloaddition reactions of azomethine ylides providing an alternative access to chiral pyrrolidines. Several classes of typical organocatalysts such as prolines, phosphoric acids, thioureas, guanidines and sulphuric acid derivatives have been used for these purposes. Various mechanistic pathways have been proposed, based on either the activation of only one reacting partner, 1,3-dipole (imine) or dipolarophile (alkene), or both of them simultaneously. While the first three classes of organocatalysts appear to afford pyrrolidines, generally, in good yields and with high levels of stereoselectivity, guanidines and sulphuric acid derivatives are less efficient, but also the least studied catalyst group. A whole range of electron deficient dipolarophiles (alkenes) have been used in these cycloaddition processes, while, regarding the dipole precursor imine, aromatic aldimines seem to be more efficient than their aliphatic equivalents. There is no doubt that the recent progress in organocatalytic cycloadditions of azomethine ylides created new possibilities for synthesis of pyrrolidine derivatives and enriched this useful synthetic methodology.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Current Organic Chemistry",
title = "Organocatalysis in Synthesis of Pyrrolidine Derivatives via Cycloaddition Reactions of Azomethine Ylides",
volume = "18",
number = "9",
pages = "1073-1096",
doi = "10.2174/1385272819999140404130229"
}

Ranđelović, J., Simić, M., Tasić, G., Husinec, S.,& Savić, V.. (2014). Organocatalysis in Synthesis of Pyrrolidine Derivatives via Cycloaddition Reactions of Azomethine Ylides. in Current Organic Chemistry
Bentham Science Publ Ltd, Sharjah., 18(9), 1073-1096.
https://doi.org/10.2174/1385272819999140404130229

Ranđelović J, Simić M, Tasić G, Husinec S, Savić V. Organocatalysis in Synthesis of Pyrrolidine Derivatives via Cycloaddition Reactions of Azomethine Ylides. in Current Organic Chemistry. 2014;18(9):1073-1096.
doi:10.2174/1385272819999140404130229 .

Ranđelović, Jelena, Simić, Milena, Tasić, Gordana, Husinec, Suren, Savić, Vladimir, "Organocatalysis in Synthesis of Pyrrolidine Derivatives via Cycloaddition Reactions of Azomethine Ylides" in Current Organic Chemistry, 18, no. 9 (2014):1073-1096,
https://doi.org/10.2174/1385272819999140404130229 . .

TY  - JOUR
AU  - Kalinić, Marko
AU  - Zloh, Mire
AU  - Erić, Slavica
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2140
AB  - Enhancer of Zeste Homolog 2 (EZH2) is a SET domain protein lysine methyltransferase (PKMT) which has recently emerged as a chemically tractable and therapeutically promising epigenetic target, evidenced by the discovery and characterization of potent and highly selective EZH2 inhibitors. However, no experimental structures of the inhibitors co-crystallized to EZH2 have been resolved, and the structural basis for their activity and selectivity remains unknown. Considering the need to minimize cross-reactivity between prospective PKMT inhibitors, much can be learned from understanding the molecular basis for selective inhibition of EZH2. Thus, to elucidate the binding of small-molecule inhibitors to EZH2, we have developed a model of its fully-formed cofactor binding site and used it to carry out molecular dynamics simulations of protein-ligand complexes, followed by molecular mechanics/generalized born surface area calculations. The obtained results are in good agreement with biochemical inhibition data and reflect the structure-activity relationships of known ligands. Our findings suggest that the variable and flexible post-SET domain plays an important role in inhibitor binding, allowing possibly distinct binding modes of inhibitors with only small variations in their structure. Insights from this study present a good basis for design of novel and optimization of existing compounds targeting the cofactor binding site of EZH2.
PB  - Springer, Dordrecht
T2  - Journal of Computer-Aided Molecular Design
T1  - Structural insights into binding of small molecule inhibitors to Enhancer of Zeste Homolog 2
VL  - 28
IS  - 11
SP  - 1109
EP  - 1128
DO  - 10.1007/s10822-014-9788-1
ER  - 

@article{
author = "Kalinić, Marko and Zloh, Mire and Erić, Slavica",
year = "2014",
abstract = "Enhancer of Zeste Homolog 2 (EZH2) is a SET domain protein lysine methyltransferase (PKMT) which has recently emerged as a chemically tractable and therapeutically promising epigenetic target, evidenced by the discovery and characterization of potent and highly selective EZH2 inhibitors. However, no experimental structures of the inhibitors co-crystallized to EZH2 have been resolved, and the structural basis for their activity and selectivity remains unknown. Considering the need to minimize cross-reactivity between prospective PKMT inhibitors, much can be learned from understanding the molecular basis for selective inhibition of EZH2. Thus, to elucidate the binding of small-molecule inhibitors to EZH2, we have developed a model of its fully-formed cofactor binding site and used it to carry out molecular dynamics simulations of protein-ligand complexes, followed by molecular mechanics/generalized born surface area calculations. The obtained results are in good agreement with biochemical inhibition data and reflect the structure-activity relationships of known ligands. Our findings suggest that the variable and flexible post-SET domain plays an important role in inhibitor binding, allowing possibly distinct binding modes of inhibitors with only small variations in their structure. Insights from this study present a good basis for design of novel and optimization of existing compounds targeting the cofactor binding site of EZH2.",
publisher = "Springer, Dordrecht",
journal = "Journal of Computer-Aided Molecular Design",
title = "Structural insights into binding of small molecule inhibitors to Enhancer of Zeste Homolog 2",
volume = "28",
number = "11",
pages = "1109-1128",
doi = "10.1007/s10822-014-9788-1"
}

Kalinić, M., Zloh, M.,& Erić, S.. (2014). Structural insights into binding of small molecule inhibitors to Enhancer of Zeste Homolog 2. in Journal of Computer-Aided Molecular Design
Springer, Dordrecht., 28(11), 1109-1128.
https://doi.org/10.1007/s10822-014-9788-1

Kalinić M, Zloh M, Erić S. Structural insights into binding of small molecule inhibitors to Enhancer of Zeste Homolog 2. in Journal of Computer-Aided Molecular Design. 2014;28(11):1109-1128.
doi:10.1007/s10822-014-9788-1 .

Kalinić, Marko, Zloh, Mire, Erić, Slavica, "Structural insights into binding of small molecule inhibitors to Enhancer of Zeste Homolog 2" in Journal of Computer-Aided Molecular Design, 28, no. 11 (2014):1109-1128,
https://doi.org/10.1007/s10822-014-9788-1 . .

TY  - JOUR
AU  - Erić, Slavica
AU  - Kalinić, Marko
AU  - Ilić, K.
AU  - Zloh, Mire
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2133
AB  - P-glycoprotein (P-gp/ABCB1) and breast cancer resistance protein (BCRP/ABCG2) are two members of the adenosine triphosphate (ATP) binding cassette (ABC) family of transporters which function as membrane efflux transporters and display considerable substrate promiscuity. Both are known to significantly influence the absorption, distribution and elimination of drugs, mediate drug-drug interactions and contribute to multiple drug resistance (MDR) of cancer cells. Correspondingly, timely characterization of the interaction of novel leads and drug candidates with these two transporters is of great importance. In this study, several computational classification models for prediction of transport and inhibition of P-gp and BCRP, respectively, were developed based on newly compiled and critically evaluated experimental data. Artificial neural network (ANN) and support vector machine (SVM) ensemble based models were explored, as well as knowledge-based approaches to descriptor selection. The average overall classification accuracy of best performing models was 82% for P-gp transport, 88% for BCRP transport, 89% for P-gp inhibition and 87% for BCRP inhibition, determined across an array of different test sets. An analysis of substrate overlap between P-gp and BCRP was also performed. The accuracy, simplicity and interpretability of the proposed models suggest that they could be of significant utility in the drug discovery and development settings.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Saudi Pharmaceutical Journal
T1  - Computational classification models for predicting the interaction of drugs with P-glycoprotein and breast cancer resistance protein
VL  - 25
IS  - 12
SP  - 955
EP  - 982
DO  - 10.1080/1062936X.2014.976265
ER  - 

@article{
author = "Erić, Slavica and Kalinić, Marko and Ilić, K. and Zloh, Mire",
year = "2014",
abstract = "P-glycoprotein (P-gp/ABCB1) and breast cancer resistance protein (BCRP/ABCG2) are two members of the adenosine triphosphate (ATP) binding cassette (ABC) family of transporters which function as membrane efflux transporters and display considerable substrate promiscuity. Both are known to significantly influence the absorption, distribution and elimination of drugs, mediate drug-drug interactions and contribute to multiple drug resistance (MDR) of cancer cells. Correspondingly, timely characterization of the interaction of novel leads and drug candidates with these two transporters is of great importance. In this study, several computational classification models for prediction of transport and inhibition of P-gp and BCRP, respectively, were developed based on newly compiled and critically evaluated experimental data. Artificial neural network (ANN) and support vector machine (SVM) ensemble based models were explored, as well as knowledge-based approaches to descriptor selection. The average overall classification accuracy of best performing models was 82% for P-gp transport, 88% for BCRP transport, 89% for P-gp inhibition and 87% for BCRP inhibition, determined across an array of different test sets. An analysis of substrate overlap between P-gp and BCRP was also performed. The accuracy, simplicity and interpretability of the proposed models suggest that they could be of significant utility in the drug discovery and development settings.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Saudi Pharmaceutical Journal",
title = "Computational classification models for predicting the interaction of drugs with P-glycoprotein and breast cancer resistance protein",
volume = "25",
number = "12",
pages = "955-982",
doi = "10.1080/1062936X.2014.976265"
}

Erić, S., Kalinić, M., Ilić, K.,& Zloh, M.. (2014). Computational classification models for predicting the interaction of drugs with P-glycoprotein and breast cancer resistance protein. in Saudi Pharmaceutical Journal
Taylor & Francis Ltd, Abingdon., 25(12), 955-982.
https://doi.org/10.1080/1062936X.2014.976265

Erić S, Kalinić M, Ilić K, Zloh M. Computational classification models for predicting the interaction of drugs with P-glycoprotein and breast cancer resistance protein. in Saudi Pharmaceutical Journal. 2014;25(12):955-982.
doi:10.1080/1062936X.2014.976265 .

Erić, Slavica, Kalinić, Marko, Ilić, K., Zloh, Mire, "Computational classification models for predicting the interaction of drugs with P-glycoprotein and breast cancer resistance protein" in Saudi Pharmaceutical Journal, 25, no. 12 (2014):955-982,
https://doi.org/10.1080/1062936X.2014.976265 . .

TY  - JOUR
AU  - Basić, J.
AU  - Kalinić, Marko
AU  - Ivković, Branka
AU  - Erić, Slavica
AU  - Milenković, Marina
AU  - Vladimirov, S.
AU  - Vujić, Zorica
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2114
AB  - Twelve 2'-hydroxy chalcones were synthesized and their in vitro antibacterial activity was tested using eight standard strains of bacteria: S. aureus (ATCC 25923), S. epidermidis (ATCC 12228), B. subtilis (ATCC 6633), M. luteus (ATCC 10240), M. flavus (ATCC 9341), E. faecalis (ATCC 29212), K. pneumoniae (NCIMB 9111) and P. aeruginosa (ATCC 27853). All 2'-hydroxy chalcones have shown moderate to good antimicrobial activity, determined by microdilution method. QSAR analysis was performed for all the cases, R-2 = 0.918 - 0.997. The results of our QSAR analysis indicate that an alternative and complementary mechanism of action is a major determinant of 2'-hydroxy chalcone antibacterial efficiency. These chalcone derivatives posses the ability to act as bidendate chelating agents whereby the ketone moiety forms a coordinate bond and the 2'-hydroxy group forms a covalent bond with a corresponding metal ion. Chelate formation can disrupt the function of bacterial metalloproteins wich may affect the further growth of bacterial cells.
PB  - Inst Materials Physics, Bucharest
T2  - Digest Journal of Nanomaterials and Biostructures
T1  - Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones
VL  - 9
IS  - 4
SP  - 1537
EP  - 1546
UR  - https://hdl.handle.net/21.15107/rcub_farfar_2114
ER  - 

@article{
author = "Basić, J. and Kalinić, Marko and Ivković, Branka and Erić, Slavica and Milenković, Marina and Vladimirov, S. and Vujić, Zorica",
year = "2014",
abstract = "Twelve 2'-hydroxy chalcones were synthesized and their in vitro antibacterial activity was tested using eight standard strains of bacteria: S. aureus (ATCC 25923), S. epidermidis (ATCC 12228), B. subtilis (ATCC 6633), M. luteus (ATCC 10240), M. flavus (ATCC 9341), E. faecalis (ATCC 29212), K. pneumoniae (NCIMB 9111) and P. aeruginosa (ATCC 27853). All 2'-hydroxy chalcones have shown moderate to good antimicrobial activity, determined by microdilution method. QSAR analysis was performed for all the cases, R-2 = 0.918 - 0.997. The results of our QSAR analysis indicate that an alternative and complementary mechanism of action is a major determinant of 2'-hydroxy chalcone antibacterial efficiency. These chalcone derivatives posses the ability to act as bidendate chelating agents whereby the ketone moiety forms a coordinate bond and the 2'-hydroxy group forms a covalent bond with a corresponding metal ion. Chelate formation can disrupt the function of bacterial metalloproteins wich may affect the further growth of bacterial cells.",
publisher = "Inst Materials Physics, Bucharest",
journal = "Digest Journal of Nanomaterials and Biostructures",
title = "Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones",
volume = "9",
number = "4",
pages = "1537-1546",
url = "https://hdl.handle.net/21.15107/rcub_farfar_2114"
}

Basić, J., Kalinić, M., Ivković, B., Erić, S., Milenković, M., Vladimirov, S.,& Vujić, Z.. (2014). Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones. in Digest Journal of Nanomaterials and Biostructures
Inst Materials Physics, Bucharest., 9(4), 1537-1546.
https://hdl.handle.net/21.15107/rcub_farfar_2114

Basić J, Kalinić M, Ivković B, Erić S, Milenković M, Vladimirov S, Vujić Z. Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones. in Digest Journal of Nanomaterials and Biostructures. 2014;9(4):1537-1546.
https://hdl.handle.net/21.15107/rcub_farfar_2114 .

Basić, J., Kalinić, Marko, Ivković, Branka, Erić, Slavica, Milenković, Marina, Vladimirov, S., Vujić, Zorica, "Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones" in Digest Journal of Nanomaterials and Biostructures, 9, no. 4 (2014):1537-1546,
https://hdl.handle.net/21.15107/rcub_farfar_2114 .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Ranđelović, Jelena
AU  - Ivković, Branka
AU  - Suteu, Cristina
AU  - Tokić-Vujošević, Zorana
AU  - Savić, Vladimir
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2098
AB  - Chiral, polysubstituted proline esters, obtained via cycloaddition reactions of azomethine ylides, were studied as organocatalysts in the Michael reaction of aldehydes/ketones and vinylsulphones. Under optimised reaction conditions employing 10 mol % of the catalyst in wet CH2Cl2, the yields of the products were generally good while the enantioselectivity varied, reaching up to 52 %.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Substituted proline derivatives as organocatalysts in the Michael reaction
VL  - 79
IS  - 7
SP  - 767
EP  - 778
DO  - 10.2298/JSC131015002J
ER  - 

@article{
author = "Jovanović, Predrag and Ranđelović, Jelena and Ivković, Branka and Suteu, Cristina and Tokić-Vujošević, Zorana and Savić, Vladimir",
year = "2014",
abstract = "Chiral, polysubstituted proline esters, obtained via cycloaddition reactions of azomethine ylides, were studied as organocatalysts in the Michael reaction of aldehydes/ketones and vinylsulphones. Under optimised reaction conditions employing 10 mol % of the catalyst in wet CH2Cl2, the yields of the products were generally good while the enantioselectivity varied, reaching up to 52 %.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Substituted proline derivatives as organocatalysts in the Michael reaction",
volume = "79",
number = "7",
pages = "767-778",
doi = "10.2298/JSC131015002J"
}

Jovanović, P., Ranđelović, J., Ivković, B., Suteu, C., Tokić-Vujošević, Z.,& Savić, V.. (2014). Substituted proline derivatives as organocatalysts in the Michael reaction. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 79(7), 767-778.
https://doi.org/10.2298/JSC131015002J

Jovanović P, Ranđelović J, Ivković B, Suteu C, Tokić-Vujošević Z, Savić V. Substituted proline derivatives as organocatalysts in the Michael reaction. in Journal of the Serbian Chemical Society. 2014;79(7):767-778.
doi:10.2298/JSC131015002J .

Jovanović, Predrag, Ranđelović, Jelena, Ivković, Branka, Suteu, Cristina, Tokić-Vujošević, Zorana, Savić, Vladimir, "Substituted proline derivatives as organocatalysts in the Michael reaction" in Journal of the Serbian Chemical Society, 79, no. 7 (2014):767-778,
https://doi.org/10.2298/JSC131015002J . .

TY  - JOUR
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Popović, Stanimir
AU  - Husinec, Suren
AU  - Maslak, Veselin
AU  - Savić, Vladimir
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1973
AB  - Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B
VL  - 54
IS  - 34
SP  - 4536
EP  - 4539
DO  - 10.1016/j.tetlet.2013.06.069
ER  - 

@article{
author = "Tasić, Gordana and Simić, Milena and Popović, Stanimir and Husinec, Suren and Maslak, Veselin and Savić, Vladimir",
year = "2013",
abstract = "Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B",
volume = "54",
number = "34",
pages = "4536-4539",
doi = "10.1016/j.tetlet.2013.06.069"
}

Tasić, G., Simić, M., Popović, S., Husinec, S., Maslak, V.,& Savić, V.. (2013). Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 54(34), 4536-4539.
https://doi.org/10.1016/j.tetlet.2013.06.069

Tasić G, Simić M, Popović S, Husinec S, Maslak V, Savić V. Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry. 2013;54(34):4536-4539.
doi:10.1016/j.tetlet.2013.06.069 .

Tasić, Gordana, Simić, Milena, Popović, Stanimir, Husinec, Suren, Maslak, Veselin, Savić, Vladimir, "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B" in Tetrahedron-Asymmetry, 54, no. 34 (2013):4536-4539,
https://doi.org/10.1016/j.tetlet.2013.06.069 . .